The Player’s Box Podcast: Episode 6 Summary
Friendship Origin Stories, Socializing on Tour & China Update
Date: September 30, 2025
Hosts: Madison Keys, Jennifer Brady, with video messages from Jessica Pegula and Desirae Krawczyk
Episode Overview
In this episode, co-hosts Madison Keys and Jennifer Brady hold down the fort while Jessica Pegula and Desirae Krawczyk check in from China with travel woes. The episode focuses on funny friendship origin stories, how the hosts socialize (or don't!) on tour, and a detailed fan Q&A about life as pro tennis players—from travel blunders to favorite candy. The tone is laid-back, self-deprecating, and full of real behind-the-scenes tennis talk.
Key Discussion Points & Insights
1. The Unforced Errors of the Week
Timestamps: 00:10–05:00
- Maddie's Unforced Error: She wasn’t prepared for Florida’s sudden heat wave, packed as if it was fall, and ended up sweating through her limited gear.
"I was literally sloshing across the court and was like slipping on my own sweat because I just quite literally didn't have enough clothes to change into." — Madison (00:46)
- Jenny’s Unforced Error: Sent a personal voice note to the wrong person—meant for Desiree, but sent to Maddie, complete with a goofy "howdy ho" greeting. Maddie replied instantly, adding to Jenny’s embarrassment.
"I was like, howdy ho. Howdy ho. Yeah. So, yeah, that was my unforced error of the week." — Jenny (03:50)
- Jess and DEZ’s Unforced Error: From China, they confess their biggest blunder—failing to set up enough VPN access, so they missed most of the episode.
"Not the worst unforced error of the week because Dez and Jess did not download enough VPNs...You actually make this episode. So you beat them." — Maddie (04:40)
2. Friendship Origins & Early Tennis Memories
Timestamps: 05:25–13:00
- How Maddie and Jenny Became Friends: Maddie spotted Jenny, a shy 10-year-old, standing alone at Everett Academy and decided she would be her new best friend. She was persistent—even chatting her up during a tournament match.
"I remember seeing you stand off in the corner, like, not speaking to anyone. And I was like, that's gonna be my new best friend." — Maddie (05:34)
"You just kept looking at me like, why is she talking to me?" — Jenny (06:42) - Early Tournament Stories: Recalling getting kicked off court during 6:30 AM practices for missing balls, having to call their parents on the landline to pick them up.
"It'd be like, yeah, I got kicked off the court again today...And he'd rip me a new one." — Jenny (09:09)
- How They Grew Apart (and Together): Different tennis paths—Maddie went pro early, Jenny played college; both homeschooled (Jenny: "I wouldn't really call it school, to be honest"), but stayed in touch.
- Jenny’s Transformation: From super-shy kid to social butterfly on tour. College life pushed her out of her shell.
"Now I don't shut up. It's like 180." — Jenny (07:15)
3. Social Dynamics on Tour
Timestamps: 13:00–16:56
- Jenny’s Reputation: Once reserved, now the most social player at tournaments—friends with everyone, constantly lingering and chatting.
"Now we walk around a tournament and it's like, Jenny! Jenny! Oh my God!" — Maddie (13:01)
- Maddie’s Style: Selective about her friends, more likely to leave the venue quickly, loyal “ride-or-die” type.
"There’s people that have wronged you that I don't speak to...I'm the grudge holder of the group." — Maddie (16:07)
- Group Dynamics: Jenny and Jess are easygoing, Dez can be feisty, Maddie holds the grudges.
4. Fan Q&A – Life as Pro Tennis Players
Timestamps: 16:56–44:50
Tournament Entry Fees
- No entry fees for WTA tournaments; players pay an annual membership, which covers tournament access and benefits.
"We don’t have entry fees. Technically we have to pay a membership fee to the WTA at the beginning of every year." — Maddie (18:32)
- ITF events (lower-level): players pay entry fees and an IPIN membership.
"The ITF circuit, you do have to pay an entry fee and it's $40." — Jenny (20:17)
Responding to Instagram DMs
- Neither reads every DM; mostly ignore negative feedback, sometimes reply to cool or positive messages.
What the Hosts Are Thankful For
- Maddie: Excited for home renovations to finish. Admits to plotting future “secret” renovations behind husband’s back.
“If my husband is listening, I’m not gonna touch anything else. It’s done...If he’s not listening, there’s still a bathroom...” — Maddie (22:08)
Do They Listen to Match Commentators?
- No; they prefer to get feedback from coaches, not commentators.
"What the commentators say is for the fans, not for the players." — Jenny (23:30) "If I’ve lost the match or played poorly, I don’t need that negativity in my life." — Maddie (23:34)
What’s in Their Bags
- Jenny: Packs light—one suitcase, one tennis bag, one backpack.
- Maddie: Packs two large rollers, sometimes more (especially after Nike gear distributions), struggles to manage the haul after European trips.
"By the end of the trip, I had, like, four, five suitcases and my tennis bag, and that was not ideal by myself to get home." — Maddie (24:19)
Favorite Candy
- Jenny: Giant list—Reese’s (any kind, especially Fast Break and seasonal), peanut M&Ms, Sour Patch Kids, Cow Tales, Twizzlers, Australian gummy snakes.
"Let me tell you. Is. Do we have a limit here?" — Jenny (26:40)
- Maddie: Chewy, sour candies—Sour Patch Kids, Sour Strips, Australian snakes, Sour Smurfs (specifically from France), and Swedish candy courtesy of physios.
"I just will eat, like, an entire bag a day...But what I have found to be very true is I had a physio from Sweden, and they have, like, the best sour candy ever." — Maddie (28:54)
Bench Selection Superstitions
- Jenny sometimes gets superstitious about which side of the umpire’s chair she sits on, especially if she's been winning from one side during a tournament.
"Sometimes I get a little superstitious...I call to finish the tournament here." — Jenny (31:53)
- The group laughs about how odd it would be to request a bench swap at the coin toss just for good vibes.
Travel Logistics on Tour
- Players are responsible for covering their own—and their entourage’s—flights, hotels, and meals (apart from a limited number of covered hotel days from the tournament).
"You're paying for your team's hotel room. So if it's however many people you have, you're paying for their room." — Maddie (37:53)
- Flights are usually booked last minute after a loss—not held in advance.
Memorable Moments & Quotes
- On Early Friendship:
"You just kept looking at me like, why is she talking to me?" — Maddie (06:42)
- On Socializing:
"We would turn a corner and everyone would be like, it's Jenny." — Maddie (13:28)
- On Grudges:
"I'm the grudge holder of the group for sure. And you know what? I'm fine with that. I'm proud of that." — Maddie (16:44)
- On Packing Failures:
"I walked off the court, I put my T shirt back on...I was like, no, no, no. Like, mom, thank you, but never again." — Jenny (40:34)
- On Tournament Mishaps:
"Three people wore it today...That's so gross." — Jenny (42:39)
- On Advice to Listeners:
"Always keep an extra outfit in your tennis bag." — Jenny (42:41)
Check-In from China: Jess & Dez
Timestamps: 45:42–49:32
- Unforced Error: VPN issues prevented them from joining the main recording.
- Favorite Candy:
"Mine's a Reese's Fast Break." — Dez (47:06)
"Probably like Sour Patch Kids are my favorite." — Jess (47:10) - Forgetting Match Outfits: Both admit to recent blunders—Dez even had her match outfit delivered to the venue by a WTA supervisor ahead of a final in Singapore this year.
- Why Friendliness Helps: “It's good to be friendly because you never know when you’ll need someone back at the tournament hotel to bring you stuff—or to sneak into your room!” (49:18)
Important Timestamps
- 00:10 – Unforced Errors of the Week
- 05:25 – Friendship Origin Stories
- 13:01 – Socializing on Tour Dynamics
- 16:56 – Fan Q&A Begins
- 18:32 – Tournament Entry Fee Rules
- 21:55 – Thankful Moments
- 23:30 – Commentary Feedback
- 24:19 – Packing for Tour
- 26:35 – Favorite Candy (Jenny’s list)
- 31:53 – Umpire Chair Superstitions
- 35:21 – Travel Logistics Explained
- 39:55 – Packing Blunders and On-Court Mishaps
- 45:42 – China Check-In: Jess & Dez
Final Thoughts
This episode is a playful and revealing look into pro tennis friendships, life on the circuit, and the small, relatable errors that keep these top athletes grounded. From accidentally sharing clothes to detailed packing routines, and the culture of helpfulness on tour, Keys, Brady, Pegula, and Krawczyk offer candid stories and genuine laughs—making the pro tour feel just a little more human.
For next week: The crew promises Jess and Dez will be back on air—VPNs willing!
To ask a fan question:
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Memorable Sign-off:
"Howdy ho!" — Maddie & Jenny (45:31)